Total synthesis of Aspidophylline A:
| Reference: | Zu,L.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 8877–8179. DOI |
| Reactions: | Ketal → Ketone • Fischer indole • Diels-Alder, Maleic anhydride • Bicyclo(222)-aza • Decarboxylation Oxidative • N-H → N-Allyl • Pd-Heck coupling • Enone → Ketone • Ketone enolate+Alkyl-X • Allyl-X+Enolate • Alkene cleavage • CompOx-Alkene/Alkene+O3 • Lactone-6 • Lactone → CarboxEster • Ether-5 • Propellane(433)-aza • Ketone → Hydrazone • Amine-6 • Bicyclo(331)-aza • Ketone → Ketal(Me) • N-Bn → N-H • N-H → N-SO2R • CarboxAmide → CarboxEster • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • N-SO2R → N-H • N-H → N-C(O)H • Alkyl-OH → Ketone-α-NR2 • |
| Reagents: | Maleic anhydride • Microwave • Orthoformate • TsOH • Na°/NH3 • BuLi(n) • Carbonate, potassium • Allyl-Br • Vinyl-I • Pd(PPh3)4 • Piperidine, pentamethyl • FeCl3 • In° • LiN(SiMe3)2 • Allyl-I • DMPU (solvent) • BH4-Na+ • OsO4, NaIO4 • BH4-Na+ • H2SO4 • Dess-Martin • Hydrazine, phenyl • Carbonate, potassium • HOMe (react) • Mg° • Formic acid • HOMe (react) • HOMe (react) • Carbodiimide • |